Acetic Acid Mixture with Hydrobromic Acid → HCID 23582254, compound

Temperature

35 °C

Into a 1L three-neck round-bottom flask with a stirrer bar, nitrogen inlet and condenser were added 20 g (78.974 mmol) of methyl-4-(2-acetyloxyethyl)-2-cyano-5-methoxypenta-2,4-dienoate, which was dissolved in 55 ml acetic acid and heated to 35° C. The solution was slowly treated over a period of ½ h with 85.21 g (237 mmol) HBr/HOAc at 35-40° C. with occasional cooling. After the addition was completed the solvents were evaporated at 40° C. and 30 mm Hg and the residue was charged while stirring with a mixture of 60 ml water and 15 ml methanol. The reaction mixture was treated with 3.3 g charcoal and heated for ½ h at 40° C. The charcoal was filtered off and the methanol was distilled off under reduced pressure. The reaction mixture was evaporated and the residue was chromatographed at 100 g silica gel using a solvent mixture of Heptane:Ethyl acetate (2:1 v/v).

1. additionAfter the addition
2. customwere evaporated at 40° C.
3. addition30 mm Hg and the residue was charged
4. additionThe reaction mixture was treated with 3.3 g charcoal
5. temperatureheated for ½ h at 40° C
6. filtrationThe charcoal was filtered off
7. distillationthe methanol was distilled off under reduced pressure
8. customThe reaction mixture was evaporated
9. customthe residue was chromatographed at 100 g silica gel using
10. additiona solvent mixture of Heptane:Ethyl acetate (2:1 v/v)

ORD record

ord-216fd3aba0b14570a41f31ee79e758bc

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07282583B2